US3962327A
Expired / Lapsed
US
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Process for the production of N-haloformylcarbamic acid halide compounds
Assignee: Bayer AG
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Filing: 1974-10-01
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Granted: 1976-06-08
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Expires: 1994-10-01
Abstract
Abstract N-haloformylcarbamic acid halide compounds of the formula ##EQU1## wherein R 1 is an optionally substituted aliphatic, cycloaliphatic, araliphatic or aromatic radical; and X is a halogen selected from fluorine, chlorine or bromine; Are prepared by a process which comprises reacting an N-haloformylcarbamic acid thio ester of the formula ##EQU2## in which R 1 and X are identified as above, and R 2 represents an optionally substituted aliphatic or araliphatic radical, With at least 2 mols of fluorine, chlorine or bromide per thiol ester group at a temperature of -20° to 100°C.
Inventors
- 👤 Hans Georg Schlee
- 👤 Klaus Sasse
- 👤 Engelbert Kuhle
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 20:18
CPC Classifications
C; C07; C07C; C07C271/00; C07C271/02
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
173 words
Process for the preparation of an N-haloformylcarbamic acid halide compound of the formula ##EQU12## in which R 1 is substituted alkyl of up to 8 carbon atoms, substituted cycloalkyl of from 5 to 7 ring carbon atoms or substituted aralkyl or aryl of from 6 to 10 carbon atoms in the aryl moiety, wherein the substituents are selected from the group consisting of halogen, alkyl and haloalkyl of from 1 to 4 carbon atoms; and X is fluorine, chlorine or bromine, which process comprises reacting an N-haloformylcarbamic acid thiol ester of the formula ##EQU13## in which R 1 and X are identified as above, and R 2 is straight-chain or branched alkyl of from 1 to 6 carbon atoms, aralkyl of from 6 to 10 carbon atoms or substituted aralkyl of from 6 to 10 carbon atoms wherein the substituent is selected from alkyl of up to 4 carbon atoms and halogen, with at least 2 moles of fluorine, chlorine or bromine per thiol ester group at a temperature of -20° to 100°C.
Claim 2
Dependent Claim
173 words
Process for the preparation of an N-haloformylcarbamic acid halide compound of the formula ##EQU12## in which R 1 is substituted alkyl of up to 8 carbon atoms, substituted cycloalkyl of from 5 to 7 ring carbon atoms or substituted aralkyl or aryl of from 6 to 10 carbon atoms in the aryl moiety, wherein the substituents are selected from the group consisting of halogen, alkyl and haloalkyl of from 1 to 4 carbon atoms; and X is fluorine, chlorine or bromine, which process comprises reacting an N-haloformylcarbamic acid thiol ester of the formula ##EQU13## in which R 1 and X are identified as above, and R 2 is straight-chain or branched alkyl of from 1 to 6 carbon atoms, aralkyl of from 6 to 10 carbon atoms or substituted aralkyl of from 6 to 10 carbon atoms wherein the substituent is selected from alkyl of up to 4 carbon atoms and halogen, with at least 2 moles of fluorine, chlorine or bromine per thiol ester group at a temperature of -20° to 100°C.
Claim 3
Dependent Claim
45 words
Process as claimed in claim 1 wherein R 1 is straight-chain or branched alkyl of from 1 to 8 carbon atoms, cycloalkyl of from 5 to 7 ring carbon atoms, or aralkyl or aryl of from 6 to 10 carbon atoms in the aryl moiety.
Claim 4
Dependent Claim
18 words
Process as claimed in claim 1 wherein R 1 is substituted alkyl of up to 8 carbon atoms.
Claim 5
Dependent Claim
21 words
Process as claimed in claim 1 wherein R 2 is straight-chain or branched alkyl of from 1 to 6 carbon atoms.
Claim 6
Dependent Claim
20 words
Process as claimed in claim 1 wherein the reaction is carried out in the presence of an inert organic solvent.
Claim 7
Dependent Claim
18 words
Process as claimed in claim 5 wherein the inert organic solvent is a hydrocarbon or a chlorinated hydrocarbon.
Claim 8
Dependent Claim
20 words
Process as claimed in claim 1 wherein the reaction is carried out at a temperature of from 0° to 50°C.
Claim 9
Dependent Claim
65 words
Process as claimed in claim 1 wherein the thiol ester of formula (II) is prepared in situ by reacting a compound of the formula ##EQU14## wherein R 1 and R 2 are identified as in claim 1 and R 3 is defined as R 2 is defined with at least an equimolar amount of fluorophosgene, phosgene, or bromophosgene at a temperature of -20° to +200°C.
Claim 10
Dependent Claim
26 words
Process as claimed in claim 8 wherein the reaction of said compound of formula (III) is carried out in the presence of an inert organic solvent.
Claim 11
Dependent Claim
20 words
Process as claimed in claim 9 wherein the inert organic solvent is a hydrocarbon, a halogenated hydrocarbon or a nitrohydrocarbon.
Claim 12
Dependent Claim
25 words
Process as claimed in claim 1 wherein N-chloroformyl-methylcarbamic acid chloride is prepared by reacting N-chloroformyl-methylcarbamic acid methylthiol ester with chlorine and recovering the desired compound.
Claim 13
Dependent Claim
27 words
Process as claimed in claim 1 wherein N-chloroformyl-sec.-butyl carbamic acid chloride is prepared by reacting N-chloroformyl-sec.-butyl carbamic acid methylthiol ester with chlorine and recovering the desired compound.
Claim 14
Dependent Claim
27 words
Process as claimed in claim 1 wherein N-chloroformyl-tert.-butyl carbamic acid chloride is prepared by reacting N-chloroformyl-tert.-butyl carbamic acid methylthiol ester with chlorine and recovering the desired compound.
Claim 15
Dependent Claim
27 words
Process as claimed in claim 1 wherein N-chloroformyl-cyclohexyl carbamic acid chloride is prepared by reacting N-chloroformyl-cyclohexyl carbamic acid methylthiol ester with chlorine and recovering the desired compound.
Claim 16
Dependent Claim
25 words
Process as claimed in claim 1 wherein N-chloroformyl-phenylcarbamic acid chloride is prepared by reacting N-chloroformyl-phenylcarbamic acid methylthiol ester with chlorine and recovering the desired compound.
Claim 17
Dependent Claim
27 words
Process as claimed in claim 1 wherein N-chloroformyl-3,4-dichlorophenyl carbamic acid chloride is prepared by reacting N-chloroformyl-3,4-dichlorophenyl carbamic acid methylthiol ester with chlorine and recovering the desired compound.
References Cited (Backward Citations)
US3536756A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-06-08 | 1979-12-08 | 1980-06-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-08 | 1983-12-08 | 1984-06-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-08 | 1987-12-08 | 1988-06-08 | $7700.00 | Window Closed / Lapsed |